Carbon Tetrachloride → HCID 86714029, compound

HRID 2206685Notes

Reaction equation

[Br:1][C:2]1[C:12]([Cl:13])=[C:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH3:23])=[CH:17][CH:16]=2)[CH:10]=[C:9]([C@H:24]2[C@H:29]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C@@H:28]([O:38][CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C@H:27]([O:46][CH2:47][C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[C@@H:26]([CH2:54][O:55][CH2:56][C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)[O:25]2)[C:3]=1[O:4][CH2:5][CH2:6]CO.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:82]([Cl:86])(Cl)(Cl)Cl>CC#N>[CH2:47]([O:46][C@H:27]1[C@H:28]([O:38][CH2:39][C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[C@@H:29]([O:30][CH2:31][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C@H:24]([C:9]2[CH:10]=[C:11]([CH2:14][C:15]3[CH:16]=[CH:17][C:18]([O:21][CH2:22][CH3:23])=[CH:19][CH:20]=3)[C:12]([Cl:13])=[C:2]([Br:1])[C:3]=2[O:4][CH2:5][CH2:6][CH2:82][Cl:86])[O:25][C@@H:26]1[CH2:54][O:55][CH2:56][C:57]1[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=1)[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1

Participants

Conditions

Temperature: 55 °C

Procedure

To a suspension of bromide 29 (1.47 g, 1.59 mmol) in CH3CN (25 mL) were added triphenylphosphine (1.1 g, 3.98 mmol) and CCl4 (2.5 mL) at r.t. The mixture was stirred at 55° C. for 3 hours. The reaction mixture was cooled to r.t and concentrated in vacuo. The residue was purified using normal phase column chromatography to provide the desired product 29-1 (1.03 g, 70%).

Workup

temperatureThe reaction mixture was cooled
concentrationconcentrated in vacuo
customThe residue was purified

Sources & evidence

ORD record: ord-a2fcdb5ac3cb404f8959cf046e552830
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371303B2

Reaction notes

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